4,10-dimethoxy-1,2,3,6b,7,8,9,12b-octahydroperylene | 1041185-08-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 4,10-dimethoxy-1,2,3,6b,7,8,9,12b-octahydroperylene
• 英文别名: 4,10-Dimethoxy-1,2,3,6b,7,8,9,12b-octahydroperylene
• CAS: 1041185-08-3
• 化学式: C₂₂H₂₄O₂
• 分子量: 320.431
• InChiKey: ZMIBSYHMUFTEJP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4,10-dimethoxy-1,2,3,6b,7,8,9,12b-octahydroperylene 在 chromium(VI) oxide 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 48.0h， 以84%的产率得到4,10-dimethoxy-1,7,8,12b-tetrahydroperylene-3,9(2H,6bH)-dione
  参考文献：
  名称：

  Synthesis of the altertoxin III framework

  摘要：

  The framework of altertoxin III, a mycotoxin produced by Alternaria fungi investing food and feed, has been synthesised for the first time. Synthetic schemes including Diels-Alder reactions of anthracene derivatives turned out to be not successful due to an aromatisation of key intermediates. This aromatisation was further investigated by DFT calculations, which showed that the aromatisation tendency is dependant from the electronic characteristics of attached substituents. A Friedel-Crafts-type hafnium triflate-catalysed dimerisation of dihydroxytetralins with subsequent benzylic oxidation furnished the target compound, which should be a suitable precursor for the synthesis of altertoxin III and related natural products. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.03.013
• 作为产物：
  描述：

  5-甲氧基-1,2,3,4-四氢-1-萘酚 在 hafnium tetrakis(trifluoromethanesulfonate) 作用下， 以 乙腈 为溶剂， 生成 4,10-dimethoxy-1,2,3,6b,7,8,9,12b-octahydroperylene
  参考文献：
  名称：

  The photophysical characterisation of novel 3,9-dialkyloxy- and diacyloxyperylenes

  摘要：

  The fundamental photophysical properties of three symmetrically substituted 3,9-perylene analogues were examined in a diverse range of solvents. All three compounds exhibited solvent-dependent fluorescence quantum yield, which was lower than that of perylene or its diimides. Whilst the absence of a large excited state dipole moment suggests that there is no preferential charge accumulation in one side of the molecules, the data suggest that intramolecular electron transfer occurs and that such an event causes additional photochemical mechanisms in chlorinated compounds where the fluorescence quantum yield is lower than in all other solvents and the values of the fluorescence decay change significantly. The dyes could be an interesting new class of fluorescence tags for labeling biomolecules and as dyes for organic photovoltaic materials. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2010.06.009

文献信息

• Tandem Friedel−Crafts Annulation to Novel Perylene Analogues
  作者：Mark A. Penick、Mathew P. D. Mahindaratne、Robert D. Gutierrez、Terrill D. Smith、Edward R. T. Tiekink、George R. Negrete

  DOI：10.1021/jo800558c

  日期：2008.8.1

  [GRAPHICS]Novel dialkyloxy- and dihydroxyoctahydroperylenes are regioselectively available via a new tandem Friedel-Crafts alkylation of tetrahydronaphthalene precursors followed by oxidative aromatization. Heating of 5-alkyloxy-1-tetralol with p-toluenesulfonic acid in sulfolane gave the corresponding octahydroperylenes in moderate yields. Studies with Lewis acids and tetralin-1,5-diol in acetonitrile at room temperature provided the 4,10-dihydroxy analogue cleanly, albeit in reduced yields. Examples of these new series of perylene analogues were partially oxidized to the corresponding contiguously aromatic, anthracene core products or fully aromatized to 3,9-dialkyloxyperylenes in good yields.